CA2532431A1 - 3-nitro-pyrazolo[1,5-a]pyrimidines substituees en position 7 - Google Patents

3-nitro-pyrazolo[1,5-a]pyrimidines substituees en position 7 Download PDF

Info

Publication number: CA2532431A1
Authority: CA; Canada
Prior art keywords: phenyl; pyrazolo; nitro; pyrimidin; compound
Prior art date: 2003-07-24
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002532431A

Other languages

English (en)

Inventor

Luis Anglada

Albert Palomer

Marta Princep

Antonio Guglietta

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ferrer Internacional SA

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-07-24

Filing date

2004-07-22

Publication date

2005-02-17

2003-07-24 Priority claimed from ES200301747A external-priority patent/ES2222814B1/es

2004-07-22 Application filed by Individual filed Critical Individual

2005-02-17 Publication of CA2532431A1 publication Critical patent/CA2532431A1/fr

Status Abandoned legal-status Critical Current

Links

FDOREHMGSRCRRM-UHFFFAOYSA-N 3-nitropyrazolo[1,5-a]pyrimidine Chemical class C1=CC=NC2=C([N+](=O)[O-])C=NN21 FDOREHMGSRCRRM-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 89
238000011282 treatment Methods 0.000 claims abstract description 5
241000124008 Mammalia Species 0.000 claims description 44
JWGYPTNGYXOXPV-UHFFFAOYSA-N 4-nitro-1h-pyrazol-5-amine Chemical compound NC=1NN=CC=1[N+]([O-])=O JWGYPTNGYXOXPV-UHFFFAOYSA-N 0.000 claims description 31
239000000203 mixture Substances 0.000 claims description 31
238000000034 method Methods 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
125000000753 cycloalkyl group Chemical group 0.000 claims description 22
102000005962 receptors Human genes 0.000 claims description 20
108020003175 receptors Proteins 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 20
-1 N-oxide-pyridyl Chemical group 0.000 claims description 15
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
201000010099 disease Diseases 0.000 claims description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
206010022437 insomnia Diseases 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
125000001072 heteroaryl group Chemical group 0.000 claims description 11
206010039897 Sedation Diseases 0.000 claims description 10
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
230000007958 sleep Effects 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 8
208000019901 Anxiety disease Diseases 0.000 claims description 7
206010021118 Hypotonia Diseases 0.000 claims description 7
230000036506 anxiety Effects 0.000 claims description 7
230000001939 inductive effect Effects 0.000 claims description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
230000036640 muscle relaxation Effects 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 6
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
206010002091 Anaesthesia Diseases 0.000 claims description 5
230000037005 anaesthesia Effects 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
206010015037 epilepsy Diseases 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
208000019116 sleep disease Diseases 0.000 claims description 5
125000000335 thiazolyl group Chemical group 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
JQUNKDYABYWJMD-UHFFFAOYSA-N 3-nitro-7-phenylpyrazolo[1,5-a]pyrimidine Chemical compound C=1C=NC2=C([N+](=O)[O-])C=NN2C=1C1=CC=CC=C1 JQUNKDYABYWJMD-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
JADSDQRFVKGFSK-UHFFFAOYSA-N n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-n-prop-2-ynylmethanesulfonamide Chemical compound C#CCN(S(=O)(=O)C)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 JADSDQRFVKGFSK-UHFFFAOYSA-N 0.000 claims description 4
AYAHJXWWEGVSSZ-UHFFFAOYSA-N n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-n-propylethanesulfonamide Chemical compound CCCN(S(=O)(=O)CC)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 AYAHJXWWEGVSSZ-UHFFFAOYSA-N 0.000 claims description 4
OWDRNRONVBSLCS-UHFFFAOYSA-N n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-n-propylpropane-2-sulfonamide Chemical compound CCCN(S(=O)(=O)C(C)C)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 OWDRNRONVBSLCS-UHFFFAOYSA-N 0.000 claims description 4
LTEAOTFMSAYDAA-UHFFFAOYSA-N n-butyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]acetamide Chemical compound CCCCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 LTEAOTFMSAYDAA-UHFFFAOYSA-N 0.000 claims description 4
QPFQAVMZFZLBPL-UHFFFAOYSA-N n-butyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]propane-2-sulfonamide Chemical compound CCCCN(S(=O)(=O)C(C)C)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 QPFQAVMZFZLBPL-UHFFFAOYSA-N 0.000 claims description 4
LVECDKCYHWOZHX-UHFFFAOYSA-N n-ethyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N(CC)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 LVECDKCYHWOZHX-UHFFFAOYSA-N 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
ANJDNYOULHETFG-UHFFFAOYSA-N 1-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]pyrrolidin-2-one Chemical compound C=1C=NC2=C([N+](=O)[O-])C=NN2C=1C(C=1)=CC=CC=1N1CCCC1=O ANJDNYOULHETFG-UHFFFAOYSA-N 0.000 claims description 3
VDLAQSNXOCWCBC-UHFFFAOYSA-N 3-nitro-7-[2-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=NC2=C([N+](=O)[O-])C=NN2C=1C1=CC=CC=C1C(F)(F)F VDLAQSNXOCWCBC-UHFFFAOYSA-N 0.000 claims description 3
SGHZHHURRAVYMJ-UHFFFAOYSA-N 3-nitro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=NC2=C([N+](=O)[O-])C=NN2C=1C1=CC=CC(C(F)(F)F)=C1 SGHZHHURRAVYMJ-UHFFFAOYSA-N 0.000 claims description 3
OQDSTHYCKSRXJE-UHFFFAOYSA-N 3-nitro-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=NC2=C([N+](=O)[O-])C=NN2C=1C1=CC=C(C(F)(F)F)C=C1 OQDSTHYCKSRXJE-UHFFFAOYSA-N 0.000 claims description 3
BWBQUMHXNLYBPX-UHFFFAOYSA-N 3-nitro-7-pyridin-4-ylpyrazolo[1,5-a]pyrimidine Chemical compound C=1C=NC2=C([N+](=O)[O-])C=NN2C=1C1=CC=NC=C1 BWBQUMHXNLYBPX-UHFFFAOYSA-N 0.000 claims description 3
KSUDOYVYUOKBGP-UHFFFAOYSA-N 4-methoxy-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-n-propylbenzenesulfonamide Chemical compound C=1C=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=CC=1N(CCC)S(=O)(=O)C1=CC=C(OC)C=C1 KSUDOYVYUOKBGP-UHFFFAOYSA-N 0.000 claims description 3
VBMXULMQUSOTQP-UHFFFAOYSA-N 4-methoxy-n-methyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 VBMXULMQUSOTQP-UHFFFAOYSA-N 0.000 claims description 3
IVMXYYGNLUTVAX-UHFFFAOYSA-N n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-n-prop-2-ynylpropane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N(CC#C)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 IVMXYYGNLUTVAX-UHFFFAOYSA-N 0.000 claims description 3
JGLMOIWGDOVJPI-UHFFFAOYSA-N n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-n-propylacetamide Chemical compound CCCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 JGLMOIWGDOVJPI-UHFFFAOYSA-N 0.000 claims description 3
MOYBQDVSWCZPDX-UHFFFAOYSA-N n-butyl-4-methoxy-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzenesulfonamide Chemical compound C=1C=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=CC=1N(CCCC)S(=O)(=O)C1=CC=C(OC)C=C1 MOYBQDVSWCZPDX-UHFFFAOYSA-N 0.000 claims description 3
SGLXDAZFGPLHFE-UHFFFAOYSA-N n-butyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzenesulfonamide Chemical compound C=1C=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=CC=1N(CCCC)S(=O)(=O)C1=CC=CC=C1 SGLXDAZFGPLHFE-UHFFFAOYSA-N 0.000 claims description 3
QDSYKTWFSCPDET-UHFFFAOYSA-N n-butyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]ethanesulfonamide Chemical compound CCCCN(S(=O)(=O)CC)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 QDSYKTWFSCPDET-UHFFFAOYSA-N 0.000 claims description 3
KCSZKOBGLTVVCH-UHFFFAOYSA-N n-butyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]methanesulfonamide Chemical compound CCCCN(S(C)(=O)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 KCSZKOBGLTVVCH-UHFFFAOYSA-N 0.000 claims description 3
BNKKFPRRLOAPQU-UHFFFAOYSA-N n-ethyl-4-methoxy-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzenesulfonamide Chemical compound C=1C=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=CC=1N(CC)S(=O)(=O)C1=CC=C(OC)C=C1 BNKKFPRRLOAPQU-UHFFFAOYSA-N 0.000 claims description 3
YONDXLUEARPVGY-UHFFFAOYSA-N n-ethyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]acetamide Chemical compound CCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 YONDXLUEARPVGY-UHFFFAOYSA-N 0.000 claims description 3
AFOZMFRIYIZUKW-UHFFFAOYSA-N n-methyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]acetamide Chemical compound CC(=O)N(C)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 AFOZMFRIYIZUKW-UHFFFAOYSA-N 0.000 claims description 3
HAEYDNGNLZALQV-UHFFFAOYSA-N n-methyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzenesulfonamide Chemical compound C=1C=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=CC=1N(C)S(=O)(=O)C1=CC=CC=C1 HAEYDNGNLZALQV-UHFFFAOYSA-N 0.000 claims description 3
IFQTVZIEMVNKNM-UHFFFAOYSA-N n-methyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)N(C)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 IFQTVZIEMVNKNM-UHFFFAOYSA-N 0.000 claims description 3
125000002971 oxazolyl group Chemical group 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
125000004306 triazinyl group Chemical group 0.000 claims description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
GQJYSOZASNUIJM-UHFFFAOYSA-N 3-nitro-7-pyridin-3-ylpyrazolo[1,5-a]pyrimidine Chemical compound C=1C=NC2=C([N+](=O)[O-])C=NN2C=1C1=CC=CN=C1 GQJYSOZASNUIJM-UHFFFAOYSA-N 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
ULUSSLBTEFSPFN-UHFFFAOYSA-N n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-n-propylbenzenesulfonamide Chemical compound C=1C=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=CC=1N(CCC)S(=O)(=O)C1=CC=CC=C1 ULUSSLBTEFSPFN-UHFFFAOYSA-N 0.000 claims description 2
GZXBONKYCDYRTF-UHFFFAOYSA-N n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-n-propylmethanesulfonamide Chemical compound CCCN(S(C)(=O)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 GZXBONKYCDYRTF-UHFFFAOYSA-N 0.000 claims description 2
DWIIKFUNNGGWHW-UHFFFAOYSA-N n-ethyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzenesulfonamide Chemical compound C=1C=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=CC=1N(CC)S(=O)(=O)C1=CC=CC=C1 DWIIKFUNNGGWHW-UHFFFAOYSA-N 0.000 claims description 2
RQOQEROSNVPEBI-UHFFFAOYSA-N n-ethyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]methanesulfonamide Chemical compound CCN(S(C)(=O)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 RQOQEROSNVPEBI-UHFFFAOYSA-N 0.000 claims description 2
VMDBRFHVMWRDGM-UHFFFAOYSA-N n-methyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)N(C)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 VMDBRFHVMWRDGM-UHFFFAOYSA-N 0.000 claims description 2
UIAFQVLHNXRPJX-UHFFFAOYSA-N n-methyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N(C)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 UIAFQVLHNXRPJX-UHFFFAOYSA-N 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
229960003692 gamma aminobutyric acid Drugs 0.000 claims 4
102000004300 GABA-A Receptors Human genes 0.000 claims 2
108090000839 GABA-A Receptors Proteins 0.000 claims 2
BSKRDHJSCGPYHC-UHFFFAOYSA-N 3-nitro-7-pyridin-2-ylpyrazolo[1,5-a]pyrimidine Chemical compound C=1C=NC2=C([N+](=O)[O-])C=NN2C=1C1=CC=CC=N1 BSKRDHJSCGPYHC-UHFFFAOYSA-N 0.000 claims 1
LWMWOVOYJMKBLA-UHFFFAOYSA-N 3-nitro-7-thiophen-2-ylpyrazolo[1,5-a]pyrimidine Chemical compound C=1C=NC2=C([N+](=O)[O-])C=NN2C=1C1=CC=CS1 LWMWOVOYJMKBLA-UHFFFAOYSA-N 0.000 claims 1
YBJIMPJNWYGNEO-UHFFFAOYSA-N 7-(furan-2-yl)-3-nitropyrazolo[1,5-a]pyrimidine Chemical compound C=1C=NC2=C([N+](=O)[O-])C=NN2C=1C1=CC=CO1 YBJIMPJNWYGNEO-UHFFFAOYSA-N 0.000 claims 1
101100134922 Gallus gallus COR5 gene Proteins 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
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230000006806 disease prevention Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 375
239000010410 layer Substances 0.000 description 114
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 79
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 74
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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HUNXMJYCHXQEGX-UHFFFAOYSA-N zaleplon Chemical compound CCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 HUNXMJYCHXQEGX-UHFFFAOYSA-N 0.000 description 8
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LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 6
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AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 5
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KHHWSXAYFRFGEB-UHFFFAOYSA-N n-butyl-n-[3-[3-(dimethylamino)prop-2-enoyl]phenyl]ethanesulfonamide Chemical compound CCCCN(S(=O)(=O)CC)C1=CC=CC(C(=O)C=CN(C)C)=C1 KHHWSXAYFRFGEB-UHFFFAOYSA-N 0.000 description 1
HIONNZZFVNQTOR-UHFFFAOYSA-N n-butyl-n-[3-[3-(dimethylamino)prop-2-enoyl]phenyl]methanesulfonamide Chemical compound CCCCN(S(C)(=O)=O)C1=CC=CC(C(=O)C=CN(C)C)=C1 HIONNZZFVNQTOR-UHFFFAOYSA-N 0.000 description 1
CQUZMBRUHUOPCL-UHFFFAOYSA-N n-butyl-n-[3-[3-(dimethylamino)prop-2-enoyl]phenyl]propane-2-sulfonamide Chemical compound CCCCN(S(=O)(=O)C(C)C)C1=CC=CC(C(=O)C=CN(C)C)=C1 CQUZMBRUHUOPCL-UHFFFAOYSA-N 0.000 description 1
UYRAIFMZSZDUCF-UHFFFAOYSA-N n-ethyl-n-[3-(3-nitropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)N(CC)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)[N+]([O-])=O)=C1 UYRAIFMZSZDUCF-UHFFFAOYSA-N 0.000 description 1
SQBCGUPFPORBQY-UHFFFAOYSA-N n-ethylethanesulfonamide Chemical compound CCNS(=O)(=O)CC SQBCGUPFPORBQY-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
238000011422 pharmacological therapy Methods 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000000163 radioactive labelling Methods 0.000 description 1
230000036385 rapid eye movement (rem) sleep Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
230000004799 sedative–hypnotic effect Effects 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000007428 synaptic transmission, GABAergic Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
208000016254 weariness Diseases 0.000 description 1
229960000820 zopiclone Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA002532431A 2003-07-24 2004-07-22 3-nitro-pyrazolo[1,5-a]pyrimidines substituees en position 7 Abandoned CA2532431A1 (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
ES200301747		2003-07-24
ES200301747A ES2222814B1 (es)	2003-07-24	2003-07-24	3-nitro-pirazolo(1,5-a)pirimidinas 7-sustituidas y composiciones y metodos relacionados.
ES200401696		2004-07-12
ES200401696A ES2245893B1 (es)	2003-07-24	2004-07-12	Mejoras en el objeto de la patente de invencion n.p200301747 que se refiere a "3-nitro-pirazolo(1,5-a)pirimidinas 7-sustituidas y composiciones y metodos relacionados".
PCT/EP2004/008207 WO2005014596A1 (fr)	2003-07-24	2004-07-22	3-nitro-pyrazolo[1,5-a]pyrimidines substituées en position 7

Publications (1)

Publication Number	Publication Date
CA2532431A1 true CA2532431A1 (fr)	2005-02-17

Family

ID=34137683

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002532431A Abandoned CA2532431A1 (fr)	2003-07-24	2004-07-22	3-nitro-pyrazolo[1,5-a]pyrimidines substituees en position 7

Country Status (15)

Country	Link
US (1)	US20070043064A1 (fr)
EP (1)	EP1648896B1 (fr)
JP (1)	JP2006528607A (fr)
KR (1)	KR20060030907A (fr)
AT (1)	ATE386040T1 (fr)
AU (1)	AU2004263277A1 (fr)
BR (1)	BRPI0412837A (fr)
CA (1)	CA2532431A1 (fr)
DE (1)	DE602004011780D1 (fr)
HR (1)	HRP20060008A2 (fr)
MX (1)	MXPA06000774A (fr)
NO (1)	NO20060586L (fr)
TW (1)	TWI252851B (fr)
UY (1)	UY28439A1 (fr)
WO (1)	WO2005014596A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20050245517A1 (en) *	2004-04-29	2005-11-03	Phil Skolnick	2-pyridinyl[7-(substituted-pyridin-4-yl) pyrazolo[1,5-a]pyrimidin-3-yl]methanones
EP1884516A1 (fr) *	2006-08-04	2008-02-06	Ferrer Internacional, S.A.	Pyrazolo[1,5-a]pyrimidines, compositions pharmaceutiques les contenant et leur utilisation
GB201223308D0 (en)	2012-12-21	2013-02-06	Univ Sunderland	Enzyme inhibitors

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE792533A (fr) *	1971-12-09	1973-06-08	Int Chem & Nuclear Corp	Nouvelles pyrazolo (1,5a) pyrimidines et leur procede de preparation
US4626538A (en) *	1983-06-23	1986-12-02	American Cyanamid Company	[7-(3-disubstituted amino)phenyl]pyrazolo[1,5-a]pyrimidines
EP0264773A1 (fr) *	1986-10-16	1988-04-27	American Cyanamid Company	4,5-Dihydro- et 4,5,6,7-tétrahydropyrazolo[1,5-a]pyrimidines
DE4333705C2 (de) *	1993-10-02	2003-10-30	Guenter Ege	Arylmethylsubstituierte Pyrazolo-azine, insbesondere 3-Arylmethylpyrazolo[1,5-a]pyrimidine und Verfahren zur Herstellung von 8-Arylmethyl-pyrazolo[5,1-c][1,2,4]triazinen
US5538977A (en) *	1995-03-17	1996-07-23	American Cyanamid Company	3-Substituted-7-[3-(imidazol-1-yl)phenyl]-pyrazolo[1,5-a]pyrimidines
AU4203500A (en) *	1999-04-06	2000-10-23	Du Pont Pharmaceuticals Company	Pyrazolopyrimidines as crf antagonists
US6399621B1 (en) *	1999-08-10	2002-06-04	American Cyanamid Company	N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1, 5-α]-pyrimidin-7-yl}phenyl)acetamide and compositions and methods related thereto
DE10153344A1 (de) *	2001-10-29	2003-05-15	Gruenenthal Gmbh	Verwendung von substituierten Pyrazolopyrimidinen als Liganden von Nucleosid-Transport-Proteinen und/oder von Purinorezeptoren

2004
- 2004-07-15 TW TW093121112A patent/TWI252851B/zh not_active IP Right Cessation
- 2004-07-22 MX MXPA06000774A patent/MXPA06000774A/es not_active Application Discontinuation
- 2004-07-22 BR BRPI0412837-0A patent/BRPI0412837A/pt not_active IP Right Cessation
- 2004-07-22 WO PCT/EP2004/008207 patent/WO2005014596A1/fr not_active Ceased
- 2004-07-22 DE DE602004011780T patent/DE602004011780D1/de not_active Expired - Lifetime
- 2004-07-22 AT AT04741222T patent/ATE386040T1/de not_active IP Right Cessation
- 2004-07-22 KR KR1020067001168A patent/KR20060030907A/ko not_active Ceased
- 2004-07-22 US US10/563,104 patent/US20070043064A1/en not_active Abandoned
- 2004-07-22 AU AU2004263277A patent/AU2004263277A1/en not_active Abandoned
- 2004-07-22 CA CA002532431A patent/CA2532431A1/fr not_active Abandoned
- 2004-07-22 EP EP04741222A patent/EP1648896B1/fr not_active Expired - Lifetime
- 2004-07-22 JP JP2006520795A patent/JP2006528607A/ja not_active Abandoned
- 2004-07-22 HR HR20060008A patent/HRP20060008A2/xx not_active Application Discontinuation
- 2004-07-26 UY UY28439A patent/UY28439A1/es unknown
2006
- 2006-02-06 NO NO20060586A patent/NO20060586L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
WO2005014596A1 (fr)	2005-02-17
MXPA06000774A (es)	2006-04-18
US20070043064A1 (en)	2007-02-22
BRPI0412837A (pt)	2006-09-26
HRP20060008A2 (en)	2006-07-31
KR20060030907A (ko)	2006-04-11
DE602004011780D1 (de)	2008-03-27
NO20060586L (no)	2006-02-06
JP2006528607A (ja)	2006-12-21
ATE386040T1 (de)	2008-03-15
EP1648896B1 (fr)	2008-02-13
UY28439A1 (es)	2004-11-08
AU2004263277A1 (en)	2005-02-17
TWI252851B (en)	2006-04-11
TW200504074A (en)	2005-02-01
EP1648896A1 (fr)	2006-04-26

Legal Events

Date	Code	Title	Description
2006-07-04	EEER	Examination request
2009-07-22	FZDE	Discontinued

Publication	Publication Date	Title
JP2022506887A (ja)	2022-01-17	窒素含有縮合複素環系ｓｈｐ２阻害剤化合物、製造方法及び使用
CA2647116C (fr)	2013-12-31	Imidazo [1, 2-b] pyridazines, leurs procedes de preparation et leur utilisation en tant que ligands du recepteur gaba
CA2532437C (fr)	2010-01-26	N-[3-(3-substitues-pyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-sulfonamides et compositions et methodes associees
CA2532431A1 (fr)	2005-02-17	3-nitro-pyrazolo[1,5-a]pyrimidines substituees en position 7
CA2659969A1 (fr)	2008-02-07	Pyrazolo[1,5-a]pyrimidines, procedes, applications et compositions
AU2006334364B2 (en)	2011-09-29	Imidazo (1,2-a)pyridin-3-yl-acetic acid hydrazides, processes for their preparation and pharmaceutical uses thereof
ES2222814B1 (es)	2005-12-01	3-nitro-pirazolo(1,5-a)pirimidinas 7-sustituidas y composiciones y metodos relacionados.
WO2006084835A1 (fr)	2006-08-17	N-(3-(imidazo[1,5-a]pyrimidin-4-yl)phenyl]sulfonamides et n-[3-(imidazo[1,5-a]pyrimidin-4-yl)phenyl]carboxamides et leur utilisation en tant que modulateurs des recepteurs gabaa
HK1083844B (en)	2009-06-19	N- [3-(3-substituted-pyrazolo[1,5-a] pyrimidin-7-yl) phenyl]-sulfonamides, and compositions, and methods related thereto
HK1127917B (en)	2010-09-24	Imidazo [1,2-b] pyridazines, their processes of preparation and their use as gaba receptor ligands
HK1123792B (en)	2010-02-26	Imidazo (1,2-a)pyridin-3-yl-acetic acid hydrazides, processes for their preparation and pharmaceutical uses thereof
HK1129105B (en)	2010-09-24	Pyrazolo[1,5-a] pyrimidines, processes, uses and compositions